Pyrrolidine → HCID 66875895, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium-tert-butoxide (0.18 g, 1.87 mmol) in toluene (2 mL) cooled to 0° C. was added tert-butyl 4-(3-(5-bromopyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.34 mmol). The mixture was degassed for 20 min. Palladium acetate (0.02 g, 0.089 mmol) and (2-biphenyl)di-tert-butylphosphine (0.06 g, 0.2 mmol) was added and the mixture was degassed for 10 min. Pyrrolidine (0.114 g, 1.6 mmol) was added and the mixture was heated at 85° C. for 15 h. The reaction was cooled and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to give the title compound (0.21 g, 35.8%). 1H NMR (500 MHz, DMSO-d6): δ 7.61 (s, 1H), 7.28 (s, 1H), 6.99 (m, 1H), 6.91 (d, J=7.25 Hz, 1H), 6.83 (m, 3H), 6.31 (s, 1H), 3.48 (m, 2H), 3.38 (m, 2H), 3.28 (m, 4H), 2.44 (m, 2H), 2.29 (m, 2H), 2.04 (m, 4H), 1.47 (s, 9H); m/z (436.2, MH+).

Provenance & Evidence